As the cover star of the July issue of MoneyCentral magazine, Kyle Hanslovan is no stranger to success. The co-founder and CEO of HUNTRESS, a sleek cybersecurity operation recently valued at $1.5 billion, Kyle is at the forefront of a revolution in cybersecurity. His journey from an ambitious hacker to a respected industry leader is nothing short of remarkable.
Kyle’s accolades are numerous: he was listed among CRN’s “Top 100 Executives of 2023,” the “Top 25 Technology Disruptors,” and Ernst & Young’s “2024 Entrepreneur of the Year.” He has also earned titles such as “award-winning cyberwarfare expert” and “elite NSA operative.” These achievements underscore his pivotal role in shaping the cybersecurity landscape.
Kyle’s career reads like an epic movie script. As a teenager, he wasn’t just another kid watching cable TV; he was a budding hacker eager to prove himself in a world full of challenges. His early years were marked by personal struggles, including an absent father and a tumultuous life with a single mother. However, these adversities only fueled his drive for success.
Finding solace and purpose in the Junior ROTC, Kyle embraced the discipline, accountability, and camaraderie it offered. The corps instilled in him values of justice, integrity, honor, and moral character, which he carried into his career. After graduating high school early, he joined the Air Force, where he managed over $10 million worth of government resources by the age of 19.
During his award-winning military career, Kyle thrived on the adrenaline of hacking global communication systems, rising through the ranks of the NSA to become one of the finest cyber warfare operators. His tech skills and knack for foiling cyber-attacks made him a formidable force. However, his contributions remained largely unseen. Seeking a more visible impact, Kyle transitioned to the private sector.
A pivotal moment came in 2014 when Kyle won DEF CON’s Capture the Flag, the nation’s premier hacking competition. Courted by Fortune 500 companies, he turned them down, focusing instead on addressing a critical gap in the cybersecurity market: the needs of small businesses. Traditional cybersecurity providers overlooked these businesses, but Kyle saw their potential and necessity.
Determined to make a difference, Kyle founded HUNTRESS, a venture dedicated to providing elite, affordable cyber protection to small and mid-sized businesses. His remote team of ethical hackers has since raised over $300 million in capital, securing hundreds of jobs and livelihoods. Today, HUNTRESS stands as a beacon of cybersecurity for the backbone of the American economy.
Now at a crossroads, Kyle reflects on his journey. Having built a successful company, he has ensured a better life for his three children and set an example of leadership. With HUNTRESS running smoothly without his constant oversight, he is ready to take on new challenges. At 38, Kyle is poised to invest in the future. Grateful for the support he received, he aims to amplify the voices of passionate creatives who seek to overhaul unjust systems. With expertise in mission strategy, culture building, and venture funding, Kyle is on the hunt for his next worthy adversaries, ready to leave an even greater legacy.
Kyle Hanslovan’s story is one of resilience, innovation, and unwavering determination. As he continues to push boundaries and challenge the status quo, the world watches eagerly to see what this cybersecurity maverick will conquer next. MoneyCentral Magazine recently caught up with Kyle to discuss his journey as an entrepreneur, and here’s what went down:
Can you tell us about the journey that led you to co-found HUNTRESS and what motivated you to focus on cybersecurity for small and mid-sized businesses?
We only have one life to live, so we’d better use it to solve problems worth solving. This thought was a major part of what inspired me to become a hacker for the US Intelligence Community. It also pushed me to leave my career supporting national security to protect the backbone of the global economy—small and mid-sized businesses (SMBs)—and square off against the cybercriminals that threatened them.
As someone who started hacking at a young age, how did your early experiences shape your approach to cybersecurity and your career in this field?
As a teen hacker in the early days of dial-up internet, most of my obsession came from the challenge and thrill of bending normal functionality to do something completely unexpected. However, I also craved what others had that I didn’t, so it’s not surprising that I spent my time bypassing licensing restrictions to play the hottest video games or use the latest software. Growing up with the mindset that hacking can be a means to get ahead helps you appreciate why some cyber adversaries often look at their illicit gains as merely a job rather than a crime. It’s also a massive reminder of how innovative my teammates and I need to be in order to stay ahead of folks with equal creativity and little to lose.
What were some of the biggest challenges you faced while building HUNTRESS from the ground up, and how did you overcome them?
When we founded HUNTRESS in 2015, two dozen multi-billion dollar cybersecurity companies already served the largest banks, healthcare firms, and government institutions across the globe. There wasn’t an obvious niche for us to claim in this enterprise market, but the businesses below the Fortune 2000 were dangerously under-protected. Despite all the clear signs that cybercriminals favored targeting these mid-market and small businesses, Silicon Valley’s venture capitalists were less than convinced. It took us years of consistent revenue growth, endless positive feedback, and the help of local angel investors to finally catch the attention of major investors and analysts in 2020.
Your background includes significant military experience and work with the NSA. How did these experiences influence your leadership style and strategic thinking in the private sector?
Cyber operations within the Air Force, and especially at the NSA, leverage small distributed teams to deliver specific valuable outcomes. The most important leadership trait I embody from this experience is my daily focus on delivering clarity by challenging our fully remote teammates when they may be prioritizing less valuable “outputs” over the unmistakably critical “outcomes” that make the greatest difference to our partners and customers. Put another way, it’s very easy to overlook that “gathering intelligence on a terrorist threat” isn’t quite the same as “thwarting a terrorist attack.” When you make this mistake in cybersecurity, companies get held for ransom, operations tend to halt, and employees might not get paid.
In 2023, you were listed among CRN’s “Top 100 Executives,” “Top 25 Technology Disruptors,” and Ernst & Young’s “2024 Entrepreneur of the Year.” What do these accolades mean to you, and how do they reflect HUNTRESS’ impact on the cybersecurity industry?
I genuinely appreciate these types of awards as they validate that all our hard work and tough times have been recognized and appreciated. However, I also have to remind myself that these accolades are lagging indicators detailing past successes and aren’t indicative of our future success. I firmly believe that challenging malicious humans requires more perspiration than inspiration (though both help), so my focus is squarely on the future and predicting where shady hackers will go next. That’s how you make a real impact on any industry.
HUNTRESS has been valued at over $1.56 billion. What do you believe has been the key to your company’s rapid growth and success?
Weak leadership would give you a strictly “by-the-numbers” answer, which might sound something like this: building a product that customers love, maintaining sound gross margins and retention, and constantly expanding our total addressable market is what has launched HUNTRESS beyond unicorn company valuation after raising $150 million in our latest funding round. Although that’s not incorrect, financial milestones alone lack the heart and soul that have quickly propelled HUNTRESS to this level. Instead, we internally rally ourselves around one annual thematic goal: How many companies can we help protect, and how much of their environment can we secure? The end result is a north star that partners and customers can get behind just as strongly as our engineers, sellers, marketers, supporting teammates, and investors. This is the real magic behind our rapid growth and success.
Given your commitment to helping small businesses, what do you think are the most pressing cybersecurity threats they face today, and how does HUNTRESS address them?
Cybercriminals are heavily investing in massive amounts of automation to target the same millions of mid-market and small businesses that HUNTRESS is trying to protect. This means that any organization, regardless of size or revenue, can become a target of opportunity. The automation used by these malicious hackers focuses on technical debt and misconfigurations in yesteryear’s technologies, as well as abusing nuances in newly adopted cloud applications and other work-from-anywhere innovations. HUNTRESS products and ethical hackers augment IT departments to educate, prevent, detect, and respond to threats against work laptops, servers, email accounts, and employees. However, we’re very direct that this isn’t a silver bullet—we’re dramatically reducing your risk but not eliminating it entirely. Similar to how a self-care routine keeps you fit, YET complex issues like cancer still pose a threat. Cybersecurity is very similar, and together, we help even the smallest teams find, treat, and overcome the “inevitable” incident before this malicious automation creates a terminal situation.
You’ve raised over $300 million in capital for HUNTRESS. What advice would you give to other entrepreneurs looking to secure funding for their ventures?
Despite all the promises from Venture Capitalists and Private Equity, I’ve rarely seen investment partners provide more value than financing. I’ve had to spend an overwhelming amount of my time forging long-standing personal relationships with potential investors well before I ever needed their help. This strategy takes a lot of proactive and predictive thought and has been a cornerstone of my strategy to build an iconic company of consequence. Before you sign a term sheet, I highly encourage you to ask yourself, “Do I truly know whether this person and firm will ride through hell with me when times get rough?” If your answer is not an overwhelming “YES,” I’d argue that you’re not truly ready to close your round.
Looking back on your career, what are some of the pivotal moments that defined your path and led you to where you are today?
Having a clearly defined, ambitious mission played a pivotal role in our journey and helped us every time our confidence wavered. Each major stumble acted as an inflection point where we could have thrown in the towel, but we’ve always risen up and protected those who needed our cybersecurity expertise. The mission to defend SMBs has also empowered dozens of the world’s greatest ethical hackers and an entire community of IT professionals and Managed Service Providers to join the Huntress team and rally behind our mission. If it’s not obvious, I firmly believe you’ll wander lost without a “north star” to guide you—in business and in life.
With HUNTRESS now a well-oiled machine, what future goals and projects do you have in mind, and how do you plan to continue making an impact in the cybersecurity industry and beyond?
As previously mentioned, cybercriminals are closely examining weaknesses in SMBs’ existing environments while also hungry to take advantage of the new digital innovations coming at the speed of AI. This presents a massive attack surface across the globe’s economic backbone, and HUNTRESS can’t protect it all despite releasing two new products in less than 12 months. As a result, we’re rapidly accelerating our research and development alongside our acquisition strategy to build and buy several new products. Expect to see innovations in Security Information and Event Management (SIEM) in the next few quarters, alongside plans to enter the Security Posture Management (SPM) markets to help our partners and customers harden their endpoints, identities, and SaaS applications. Cybercriminals don’t sleep. Neither do we.
